Palladium-Catalyzed sp3 C–H Nitration of 8-Methylquinolines
State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, People’s Republic of China
J. Org. Chem., 2015, 80 (11), pp 5973–5978
DOI: 10.1021/acs.joc.5b00735
Publication Date (Web): May 20, 2015
Copyright © 2015 American Chemical Society
*E-mail: ykuiliu@zjut.edu.cn.
Abstract
Palladium-catalyzed nitration of 8-methylquinolines with t-BuONO to give 8-(nitromethyl)quinolines in moderate to excellent yields has been developed involving an sp3 C–H bond activation. The resulting (nitromethyl)quinolines could be selectively reduced to (1,2,3,4-tetrahydroquinolin-8-yl)methanamines by NaBH4 in the presence of a catalytic amount of NiCl2·6H2O.
Supporting Information
Copies of 1H NMR and 13C NMR spectra of the products. The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.joc.5b00735.
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